Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 139 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A virtual Halloween running event offering 5k to ultra distances, mailed medals for paid entries and a free Strava option for results-only participation.
A virtual Halloween run offering distances from 5k to ultra worldwide, with paid entries eligible for a themed medal after verification and free Strava entries recorded in the results.
A virtual Halloween run offering distances from 5k to Ultra, with virtual bibs, themed medals, and options for paid or free Strava entry.
Virtual Halloween run open worldwide with distances from 5k to Ultra; paid entrants receive mailed medals while free participants can appear on the results via the organiser's Strava club.
Backyard Ultra in Bristol asks runners to complete a four mile loop each hour for six hours, with a beer, finisher goody bundle, water station and prizes for top male and female.
A virtual Halloween run on 25 October 2026 offering 5k, 10k, half, marathon and ultra distances with virtual bibs and paid medals available after verification.
A 20 km multi terrain fell race on 25 October 2026 across varied Mendip landscapes with 420 m of climb, drinks stations en route and veteran prize categories.
A 9.6 km fell race with 485 m ascent near Abergavenny on 31 October 2026; full WFRA kit is required and parking at the pub is very limited.
November 2026
A 10 mile off-road trail run in Stonehouse near Stroud on 1 November 2026, with an initial uphill mile, muddy undulating trails, a finisher medal and a 2 hour 30 minute cutoff.
Approximately 7 mile multi-terrain race from Risca Leisure Centre to Twmbarlwm and back, with about 1000 ft ascent; entries listed via Entry Central.
A multi-terrain 12 km off-road race from Barton Farm Country Park with a river crossing, chip timing, prizes and team awards, raising funds for Alzheimer's Support.
A ten mile cross country race in Chipping Sodbury with muddy, varied terrain and water obstacles. Held on Remembrance Sunday and preceded by a commemorative silence, it draws around 1300 runners.
Night and day off road 5 km and 10 km trail races around the Bath Skyline, plus a daytime kids 500 m and a canicross wave, with marked routes and finish medals.
Timed lap event in Cardiff Bay offering flexible start times and distances from one 5.3 km lap up to multi lap ultra within a 7 hour limit.
A Movember charity run at Ashton Court Park offering 1.5k, 5k, 10k and half marathon options with chip timing, medals and headbands, mixed path and trail terrain, some hilly sections, and on course refreshments.
Annual trail races from Bath Racecourse featuring a two lap hilly half and a one lap Ultra 10 km on rough, scenic terrain with aid stations and on course cut offs.
A 5.7 km fell race in Llanfoist with 485 m of ascent, limited to 120 runners and supporting local woodland restoration.
Timed multi-lap event at Parc Taf Bargoed offering distances from a single 5.3 km lap up to an ultra, with bespoke medals and a no medal entry option.